GB1383088A - Pharmacologically active quinaldamide derivatives - Google Patents
Pharmacologically active quinaldamide derivativesInfo
- Publication number
- GB1383088A GB1383088A GB3099072A GB3099072A GB1383088A GB 1383088 A GB1383088 A GB 1383088A GB 3099072 A GB3099072 A GB 3099072A GB 3099072 A GB3099072 A GB 3099072A GB 1383088 A GB1383088 A GB 1383088A
- Authority
- GB
- United Kingdom
- Prior art keywords
- compounds
- alkyl
- quinaldamide
- derivatives
- prepared
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- ZEXKKIXCRDTKBF-UHFFFAOYSA-N quinoline-2-carboxamide Chemical class C1=CC=CC2=NC(C(=O)N)=CC=C21 ZEXKKIXCRDTKBF-UHFFFAOYSA-N 0.000 title abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 238000006243 chemical reaction Methods 0.000 abstract 2
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 abstract 1
- ULRPISSMEBPJLN-UHFFFAOYSA-N 2h-tetrazol-5-amine Chemical compound NC1=NN=NN1 ULRPISSMEBPJLN-UHFFFAOYSA-N 0.000 abstract 1
- -1 NH 2 Chemical group 0.000 abstract 1
- 125000001931 aliphatic group Chemical group 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000003282 alkyl amino group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004663 dialkyl amino group Chemical group 0.000 abstract 1
- 150000002148 esters Chemical class 0.000 abstract 1
- PWOYTBYNBYNZCO-UHFFFAOYSA-N ethyl quinoline-2-carboxylate Chemical class C1=CC=CC2=NC(C(=O)OCC)=CC=C21 PWOYTBYNBYNZCO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000000543 intermediate Substances 0.000 abstract 1
- 239000000203 mixture Substances 0.000 abstract 1
- LOAUVZALPPNFOQ-UHFFFAOYSA-N quinaldic acid Chemical compound C1=CC=CC2=NC(C(=O)O)=CC=C21 LOAUVZALPPNFOQ-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 230000001225 therapeutic effect Effects 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D215/00—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems
- C07D215/02—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom
- C07D215/16—Heterocyclic compounds containing quinoline or hydrogenated quinoline ring systems having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen atoms or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D215/48—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
- Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
- Quinoline Compounds (AREA)
- Medicinal Preparation (AREA)
Abstract
1383088 Quinaldamide derivatives ALLEN & HANBURYS Ltd 12 June 1973 [3 July 1972] 30990/72 Heading C2C The invention comprises compounds of formula their pharmaceutically acceptable salts, and esters of the OH-compounds with aliphatic acids, wherein R 1 , R 2 , R 3 are each H, alkyl, NO 2 , halogen, NR 4 R 5 or OR 4 ; R 4 , R 5 are each H, alkyl (possibly substituted by OH, alkoxy, NH 2 , alkylamino, dialkylamino or aryl), or NR 4 R 5 forms a heterocyclic ring; and R 6 is H or alkyl. In examples, these compounds are prepared by reacting the corresponding quinaldic acid (or acid chloride) with 5-aminotetrazole, or by standard reactions for converting one substituent group (or I) into another. Intermediates otherwise prepared are the correspondingly substituted ethyl quinaldates. Therapeutic compositions which inhibit the release of spasmogeric substances arising from antigen-antibody reactions, comprise compounds of the above formula, which may be administered orally or by inhalation.
Priority Applications (22)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3099072A GB1383088A (en) | 1972-07-03 | 1972-07-03 | Pharmacologically active quinaldamide derivatives |
IE978/73A IE37795B1 (en) | 1972-07-03 | 1973-06-14 | Pharmacologically active quinaldamide derivatives |
ZA734041A ZA734041B (en) | 1972-07-03 | 1973-06-14 | Pharmacologically active compounds |
IL42513A IL42513A (en) | 1972-07-03 | 1973-06-15 | N-(1h-tetrazol-5-yl)-quinaldamide derivatives,their production and pharmaceutical compositions containing them |
CS734384A CS193474B2 (en) | 1972-07-03 | 1973-06-18 | Method of producing n-/5-tetrazolyl/amides of quinaldine acids |
AU57099/73A AU473752B2 (en) | 1972-07-03 | 1973-06-19 | Pharmacologically active compounds |
HUAE386A HU168474B (en) | 1972-07-03 | 1973-06-21 | |
BE132551A BE801246A (en) | 1972-07-03 | 1973-06-21 | NEW DERIVATIVES OF QUINALDIIC ACID AND THEIR PREPARATION |
US05/372,027 US3932416A (en) | 1972-07-03 | 1973-06-21 | N-tetrazolyl quinaldamides |
CA174,765A CA1012146A (en) | 1972-07-03 | 1973-06-22 | Tetrazolyl quinaldamides |
CH920573A CH592081A5 (en) | 1972-07-03 | 1973-06-25 | |
SE7309000A SE405477B (en) | 1972-07-03 | 1973-06-26 | PROCEDURE FOR THE PREPARATION OF TETRAZOLYL-KINALDINIC ACID DERIVATIVES WITH PHARMACOLOGICAL EFFECT |
DE2332731A DE2332731A1 (en) | 1972-07-03 | 1973-06-27 | QUINOLINE-CARBONIC ACID (2) COMPOUNDS, PROCESS FOR THEIR MANUFACTURING AND MEDICINAL PREPARATIONS CONTAINING SUCH COMPOUNDS |
AT570873A AT328449B (en) | 1972-07-03 | 1973-06-28 | PROCESS FOR THE PREPARATION OF NEW QUINOLINE CARBONIC ACID (2) COMPOUNDS AND THEIR ESTERS AND SALT |
PH14792A PH9997A (en) | 1972-07-03 | 1973-07-02 | Pharmacologically active n(1h-tetrazol-5-yl)quinaldamide compounds and compositions containing them |
LU67918A LU67918A1 (en) | 1972-07-03 | 1973-07-02 | |
ES416495A ES416495A1 (en) | 1972-07-03 | 1973-07-02 | N-tetrazolyl quinaldamides |
NO2705/73A NO137899C (en) | 1972-07-03 | 1973-07-02 | ANALOGICAL PROCEDURE FOR THE PREPARATION OF THERAPEUTIC ACTIVE N (1H-TETRAZOL-5-YL) -KINAL DAMIDES |
FR7324350A FR2247241B1 (en) | 1972-07-03 | 1973-07-03 | |
NL7309226A NL7309226A (en) | 1972-07-03 | 1973-07-03 | |
JP48075190A JPS4962486A (en) | 1972-07-03 | 1973-07-03 | |
US05/605,036 US4034075A (en) | 1972-07-03 | 1975-08-15 | Quinaldic acid derivatives |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3099072A GB1383088A (en) | 1972-07-03 | 1972-07-03 | Pharmacologically active quinaldamide derivatives |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1383088A true GB1383088A (en) | 1975-02-05 |
Family
ID=10316264
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3099072A Expired GB1383088A (en) | 1972-07-03 | 1972-07-03 | Pharmacologically active quinaldamide derivatives |
Country Status (20)
Country | Link |
---|---|
US (1) | US3932416A (en) |
JP (1) | JPS4962486A (en) |
AT (1) | AT328449B (en) |
AU (1) | AU473752B2 (en) |
BE (1) | BE801246A (en) |
CH (1) | CH592081A5 (en) |
CS (1) | CS193474B2 (en) |
DE (1) | DE2332731A1 (en) |
ES (1) | ES416495A1 (en) |
FR (1) | FR2247241B1 (en) |
GB (1) | GB1383088A (en) |
HU (1) | HU168474B (en) |
IE (1) | IE37795B1 (en) |
IL (1) | IL42513A (en) |
LU (1) | LU67918A1 (en) |
NL (1) | NL7309226A (en) |
NO (1) | NO137899C (en) |
PH (1) | PH9997A (en) |
SE (1) | SE405477B (en) |
ZA (1) | ZA734041B (en) |
Families Citing this family (14)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
GB1433774A (en) * | 1973-02-26 | 1976-04-28 | Allen & Hanburys Ltd | Heterocyclic compounds apparatus for conveying articles |
US4156726A (en) * | 1974-12-07 | 1979-05-29 | Fisons Limited | 4-Oxo-2-carboxyl quinoline derivatives used as antiallergic compounds |
US4147694A (en) * | 1977-02-07 | 1979-04-03 | Riker Laboratories, Inc. | 8-(1H-Tetrazol-5-yl-carbamoyl)quinoline compounds |
US4186201A (en) * | 1977-02-07 | 1980-01-29 | Riker Laboratories, Inc. | Methods of using 8(tetrazol-5-ylcarbamoyl)isoquinoline compounds |
US4474792A (en) * | 1979-06-18 | 1984-10-02 | Riker Laboratories, Inc. | N-Tetrazolyl benzamides and anti-allergic use thereof |
ZA811492B (en) * | 1980-03-05 | 1982-10-27 | Glaxo Group Ltd | Amidotetrazole compounds and processes for their preparation |
JPS61197558A (en) * | 1985-02-25 | 1986-09-01 | Nippon Chemiphar Co Ltd | Novel quinaldic acid amide derivative and production thereof |
US4772703A (en) * | 1986-01-27 | 1988-09-20 | American Home Products Corporation | 2-(phenoxymethyl)-quinazolines as antiallergic and antiinflammatory agents |
BG92674A (en) * | 1989-08-11 | 1993-12-24 | David Roberts | METHOD FOR OBTAINING QUINOLINE DERIVATIVES |
US5028707A (en) * | 1989-11-20 | 1991-07-02 | Board Of Regents, University Of Texas | 4-hydroxyquinaldic acid derivatives |
GB9010394D0 (en) * | 1990-05-09 | 1990-06-27 | Ici Plc | Heterocyclic compounds |
AU7080198A (en) * | 1997-04-25 | 1998-11-24 | Takeda Chemical Industries Ltd. | Cell differentiation inducing amide derivatives, their production and use |
WO2001012608A1 (en) * | 1999-08-18 | 2001-02-22 | Nippon Soda Co., Ltd. | Quinoline compounds and process for producing the same |
FR2827599A1 (en) * | 2001-07-20 | 2003-01-24 | Neuro3D | Treating central nervous system disorders, e.g. anxiety, depression, schizophrenia or pain, using new or known 2-substituted quinoline or quinoxaline derivatives having xanthenuric acid modulating action |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3391146A (en) * | 1964-11-10 | 1968-07-02 | Bristol Myers Co | Nu-substituted carbamates and thiocarbamates of 2-quinolinemethanols |
-
1972
- 1972-07-03 GB GB3099072A patent/GB1383088A/en not_active Expired
-
1973
- 1973-06-14 IE IE978/73A patent/IE37795B1/en unknown
- 1973-06-14 ZA ZA734041A patent/ZA734041B/en unknown
- 1973-06-15 IL IL42513A patent/IL42513A/en unknown
- 1973-06-18 CS CS734384A patent/CS193474B2/en unknown
- 1973-06-19 AU AU57099/73A patent/AU473752B2/en not_active Expired
- 1973-06-21 HU HUAE386A patent/HU168474B/hu unknown
- 1973-06-21 BE BE132551A patent/BE801246A/en unknown
- 1973-06-21 US US05/372,027 patent/US3932416A/en not_active Expired - Lifetime
- 1973-06-25 CH CH920573A patent/CH592081A5/xx not_active IP Right Cessation
- 1973-06-26 SE SE7309000A patent/SE405477B/en unknown
- 1973-06-27 DE DE2332731A patent/DE2332731A1/en active Pending
- 1973-06-28 AT AT570873A patent/AT328449B/en not_active IP Right Cessation
- 1973-07-02 LU LU67918A patent/LU67918A1/xx unknown
- 1973-07-02 NO NO2705/73A patent/NO137899C/en unknown
- 1973-07-02 PH PH14792A patent/PH9997A/en unknown
- 1973-07-02 ES ES416495A patent/ES416495A1/en not_active Expired
- 1973-07-03 NL NL7309226A patent/NL7309226A/xx not_active Application Discontinuation
- 1973-07-03 JP JP48075190A patent/JPS4962486A/ja active Pending
- 1973-07-03 FR FR7324350A patent/FR2247241B1/fr not_active Expired
Also Published As
Publication number | Publication date |
---|---|
NL7309226A (en) | 1974-01-07 |
DE2332731A1 (en) | 1974-03-07 |
NO137899B (en) | 1978-02-06 |
LU67918A1 (en) | 1973-09-05 |
IL42513A0 (en) | 1973-08-29 |
IE37795B1 (en) | 1977-10-12 |
CS193474B2 (en) | 1979-10-31 |
JPS4962486A (en) | 1974-06-17 |
SE405477B (en) | 1978-12-11 |
IL42513A (en) | 1976-12-31 |
ZA734041B (en) | 1974-05-29 |
AT328449B (en) | 1976-03-25 |
FR2247241B1 (en) | 1976-12-31 |
HU168474B (en) | 1976-05-28 |
NO137899C (en) | 1978-05-16 |
CH592081A5 (en) | 1977-10-14 |
AU5709973A (en) | 1974-12-19 |
US3932416A (en) | 1976-01-13 |
IE37795L (en) | 1974-01-03 |
FR2247241A1 (en) | 1975-05-09 |
PH9997A (en) | 1976-07-13 |
BE801246A (en) | 1973-12-21 |
ES416495A1 (en) | 1976-06-01 |
AU473752B2 (en) | 1976-07-01 |
ATA570873A (en) | 1975-06-15 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
PS | Patent sealed [section 19, patents act 1949] | ||
PCNP | Patent ceased through non-payment of renewal fee |